pyrimethanil (Ref: SN 100309) ** ZK 100309 ** Translations

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GENERAL INFORMATION

Description: A fungicide used to control grey mould on fruit, vegetables and ornamentals, and leaf scab on pome fruit

Introduction: 1998, USA

EC Directive 1107/2009 (repealing 91/414):

Status	Annex 1
Dossier rapporteur/co-rapporteur	Austria
Date inclusion expires	31/05/2017

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia

General status:

Pesticide type	Fungicide
Substance group	Anilinopyrimidine
Substance origin	Synthetic
Mode of action	Protective action with some curative properties
CAS RN	53112-28-0
EC number	414-220-3
CIPAC number	714
US EPA chemical code	288201
Chiral molecule	No
Chemical formula	C12H13N3
SMILES	n1c(cc(nc1Nc2ccccc2)C)C
International Chemical Identifier (InChI)	InChI=1/C12H13N3/c1-9-8-10(2)14-12(13-9)15-11-6-4-3-5-7-11/h3-8H,1-2H3,(H,13,14,15)
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	199.11
IUPAC Name	N-(4,6-dimethylpyrimidin-2-yl)aniline
CAS Name	4,6-dimethyl-N-phenyl-2-pyrimidinamine
Other status information	-
Herbicide Resistance Classification (HRAC)	Not applicable
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	9
Physical state	Colourless crystals
Related substances & organisms	propylene glycol chlorothalonil

Formulations:

Property	Value
Example manufacturers of products using this active	BASF
Example products using this active	Scala Walabi
UK LERAP status	Broadcast Air Assisted LERAP
Formulation and application details	Often supplied as a soluble concentrate that is mixed with water and used as a spray.

ENVIRONMENTAL FATE

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		121	A5	Moderate
Solubility - In organic solvents at 20oC (mg l-1)		23700	A5 - n-Hexane	-
		412300	A5 - Toluene	-
		388800	A5 - Acetone	-
		616900	A5 - Ethyl acetate	-
Melting Point (oC)		96.3	A5	-
Boiling Point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		189.9	A5	-
Flashpoint (oC)		Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	6.92 X 1002	Calculated	-
	Log P	2.84	A5	Moderate
Bulk density (g ml-1)/Specific gravity		1.19	A5	-
Dissociation constant (pKa) at 25oC		3.52	A5	-
		Note: Weak base
Vapour pressure at 25oC (mPa)		1.1	A5	Volatile
Henry's law constant at 25oC (Pa m3 mol-1)		3.60 X 10-03	B5	Non-volatile
Henry's law constant at 20oC (dimensionless)		7.42 X 10-07	Q2	Moderately volatile
GUS leaching potential index		2.65	Calculated	Transition state
SCI-GROW groundwater index (µg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.90 X 10-01	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution: 205nm = 16280, 211nm = 13450, 229nm = 4870, 271nm = 27200; [Acidic solution: 205nm = 16450, 245nm = 12260, 260nm = 14620, 317nm = 5300	A5	-
Surface tension (mN m-1)		61.51	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	55	A5	Moderately persistent
	DT50 (lab at 20oC)	55	A5	Moderately persistent
	DT50 (field)	29.5	A5	Non-persistent
	DT90 (lab at 20oC)	174.5	A5	-
	DT90 (field)	114	A5	-
	Note	EU dossier lab studies DT50 range 27.9-71.8 days, DT90 range 93-238 days; field studies DT50 range 23-54 days, DT90 range 82-180 days
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5	Stable
	Note	Not significant degradation route
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	Very persistent
	Note	Stable pH 5 to pH 9 at 22 degC
Water-Sediment DT50 (days)		80	A5	Moderately fast
Water phase only DT50 (days)		16.5	A5	Slow

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	3.97	A5	Moderately mobile
	Kfoc	301
	1/n	0.868
	Notes and range	EU dossier kf range 2.51-7.83, Kfoc range 75-500 mL/g, 1/n range 0.85-0.9, Soils=5
pH sensitivity		Slight tendency of increasing adsorption with decreasing pH

Key metabolites:

Metabolite		Formation Medium	Estimated Maximum Occurrence Fraction	91/414 Relevancy
2-amino-4,6-dimethylpyrimidine (Ref: AE-F1312593)		Soil	0.115	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation Medium / Rate	Estimated Maximum Occurrence Fraction	Metabolising Enzymes
(2-(4-hydroxyanilino)-4,6-dimethylpyrimidine	-	Animal	-	-
2-anilino-4,6-dimethylpyrimidin-5-ol	-	Animal	-	-
2-amino-4,6-dimethyl-pyrimidine	-	Soil	-	-

ECOTOXICOLOGY

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	Low risk	A5 Based on LogP < 3	High potential
	CT50 (days)	-		-
Bioaccumulation potential		-	Calculated	Low
Mammals - Acute oral LD50 (mg kg-1)		4150	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	> 139	B5 Rat	Moderate
	(ppm diet)	> 900		-
Birds - Acute LD50 (mg kg-1)		> 2000	A5 Anas platyrhynchos	Moderate
Birds - Short term dietary (LC50/LD50)		> 5200 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		10.56	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		1.6	F4 Oncorhynchus mykiss, LOEC	-
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		2.9	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.94	A5 Daphnia magna	-
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1)		4.0	A5 Chironomus riparius	Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		-	-	-
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		7.8	F4 Lemna gibba	Moderate
Algae - Acute 72 hour EC50, growth (mg l-1)		1.2	A5 Raphidocelis subcapitata	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees - Acute 48 hour LD50 (µg bee-1)		> 100	A5 Contact	Moderate
Earthworms - Acute 14 day LC50 (mg kg-1)		313	A5 Eisenia foetida, corr	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		4.12	A5 Eisenia foetida, corr	Moderate
Other soil macro-organisms - e.g. Collembola	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	63 18	Mortality Fecundity Dose: 1 kg ha-1 A5 Aphidius rhopalosiphi, adult	Moderately harmful
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	38 52	Mortality Fecundity Dose: 1.04 kg ha-1 A5 Typhlodromus pyri	Moderately harmful
Soil micro-organisms		Nitrogen mineralisation: No significant effect [Dose: 1.08 mg kg-1 soil] Carbon mineralisation: No significant effect [Dose: 10.8 mg kg-1 soil]	A5	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Mammals - Acute oral LD50 (mg kg-1)		4150	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 5000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 1.98	A5 Rat (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.17	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.12	A5 Rat, SF=100	-
Dermal penetration studies (%)		1.0-20.0	A5 concentration dependant	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	No unacceptable risks to bystanders identified
	Occupational	No unacceptable risks to operators or other workers identified
Examples of European MRLs (mg kg-1)	Value	Wine grapes: 3.0; Apples: 1.0; Fodder peas: 0.3
	Note	A5 EU dossier proposals For the EU pesticides database click here
Drinking Water MAC (µg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
	-					-
General human health issues		Possible liver, kidney, adrenals, bladder and thyroid toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		Not explosive
CLP classification 2013		-
EC Risk Classification		N - Dangerous for the environment: R51, R53
EC Safety Classification		-
WHO Classification		III	-	Slightly hazardous
US EPA Classification (formulation)		IV	-	Caution - Not acutely toxic
UN Number		Usually 3077
Waste disposal & packaging		-

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